In one example of a hydraulic operating device for a bicycle hydraulic brake, a piston is moved in a hydraulic cylinder from an initial position to an actuated position when an operating portion such as a brake lever is pivoted. Movement of the piston discharges fluid (oil, for example) from the hydraulic cylinder to drive a piston in a brake caliper, which is connected to the hydraulic cylinder by a hydraulic hose. This generates a braking force with the brake caliper.